The compound shown is converted to its sodium salt with sodium hydroxide, heated with $CO X_{2}$ at 400 K and 4-7 atm, and acidified. The product is then treated with acetic anhydride and a trace of acid. Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

The compound is phenol. Kolbe-Schmitt carboxylation of sodium phenoxide followed by acidification gives 2-hydroxybenzoic acid. Acetylation of its phenolic hydroxyl group with acetic anhydride then gives 2-acetoxybenzoic acid (aspirin). Structure B is the intermediate, and phenyl acetate has lost the carboxyl group.

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The compound shown is converted to its sodium salt with sodium hydroxide, heated with COX2​ at 400 K and 4-7 atm, and acidified. The product is then treated with acetic anhydride and a trace of acid. Which structure is the final product?

Answer: A

More questions on Acidity and reactions of drawn phenols

The compound shown is converted to its sodium salt with sodium hydroxide, heated with $CO X_{2}$ at 400 K and 4-7 atm, and acidified. The product is then treated with acetic anhydride and a trace of acid. Which structure is the final product?